Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
Studies of the Organic Reactions of Metal Carbonyls. XIV. The Reaction of Potassium Iron Carbonylates with Isoprene
Yoshinobu TakegamiYoshihisa WatanabeIsao KanayaTakeaki MitsudoToshiharu OkajimaYoshihiko MorishitaHiromitsu Masada
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1968 Volume 41 Issue 12 Pages 2990-2994


The reaction between potassium iron carbonylates (KHFe(CO)4, K2Fe(CO)4 and K2Fe2(CO)8) and isoprene has been studied. Isoprene is reduced at room temperature to give three olefins (3-methyl-1-butene (I), 2-methyl-1-butene (II), and 2-methyl-2-butene (III)). The reaction conditions (solvents, atmospheres, additives such as water) have a great effect on the yield and distribution of the olefins. Under carbon monoxide in the presence of water, the reduction is highly promoted, giving 2 mol/mol-Fe(CO)42− of the olefins. The percentage of II is almost constant (about 15%) in any case, but the percentages of I and III, very dependent on the conditions, change in the 3–40 and 50–80% ranges respectively. The reaction is suggested to proceed via some kinds of σ- and π-allyl iron carbonyl complexes. Under carbon monoxide the carbonylation of isoprene also occurs.

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